Methanol → {1-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-Purin-6-yl]-ethyl}-isopropylamine

HRID 1246818Notes

Reaction equation

HRID 1246818 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:25](=O)[CH3:26])=[CH:4][CH:3]=1.[CH:28]([NH2:31])([CH3:30])[CH3:29].CO.[BH4-].[Na+]>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[CH:25]([NH:31][CH:28]([CH3:30])[CH3:29])[CH3:26])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 4311764Sodium borohydrideHCID 219057891-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-ethanone

Product 1

HCID 21905829{1-[9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-9H-Purin-6-yl]-ethyl}-isopropylamine

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purin-6-yl]-ethanone I-(15A-1)a (16 mg, 0.038 mmol) and isopropylamine (6.5 μl, 0.076 mmol) in methylene chloride (0.3 ml) was stirred at room temperature and to it was added titanium(IV) isopropoxide (34 μl, 0.114 mmol). The reaction mixture was stirred for 3 hours and then methanol (0.5 ml) was added followed by sodium borohydride (5 mg). When the reaction was shown to be complete by LC/MS it was purified by TLC preparative plate using 10% methanol/methylene chloride with 1% ammonium hydroxide as the solvent to obtain title compound 15A-1. A solution of the material in methylene chloride was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hydrochloride salt of compound 15A-1 (5.9 mg): +ESI MS (M+1) 460.5; 1H NMR (500 MHz, CD3OD) δ 9.08 (s, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.64 (s, 1H), 7.59–7.48 (m, 3H), 7.41 (d, J=8.8 Hz, 2H), 5.38 (q, J=6.2 Hz, 1H), 3.45 (septuplet, J=6.5 Hz, 1H), 1.84 (d, J=6.7 Hz, 3H), 1.43 (d, J=6.7 Hz, 3H), 1.41, (d, J=6.2 Hz, 3H).

Workup

  1. customwas purified by TLC preparative plate

Sources & evidence

ORD record
ord-7979b3b5585741b894f637b643e167d8
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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